Phosphorescent emitters containing dibenzo[1,4]azaborinine structure

• US 9,231,218 B2
• Filed: 03/13/2013
• Issued: 01/05/2016
• Est. Priority Date: 07/10/2012
• Status: Active Grant

• Current Assignee: Universal Display Corporation
• Original Assignee: Universal Display Corporation
• Inventors: Lin, Chun, Xia, Chuanjun
• Primary Examiner(s): Blackwell, Gwendolyn
• Assistant Examiner(s): Zhang, Ruiyun
• Application Number:
  US13/798,935
• Publication Number:
  US 20140014922A1
• Time in Patent Office: 1,028 Days
• Field of Search: 428/690, 428/917, 540/1, 540/4, 540/13, 548/405, 548/103, 549/213, 549/4, 564/8, 546/4
• US Class Current: 1/1
• CPC Class Codes: C09K 11/06 containing organic luminescent materials
• CPC Class Codes: C09K 2211/1007 Non-condensed systems
• CPC Class Codes: C09K 2211/1029 containing one nitrogen atom as the heteroatom
• CPC Class Codes: C09K 2211/104 with other heteroatoms
• CPC Class Codes: C09K 2211/1044 containing two nitrogen atoms as heteroatoms
• CPC Class Codes: C09K 2211/185 of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
• CPC Class Codes: H05B 33/14 characterised by the chemical or physical composition or the arrangement of the electroluminescent material , or by the simultaneous addition of the electroluminescent material in or onto the light source
• CPC Class Codes: H10K 2101/10 Triplet emission
• CPC Class Codes: H10K 50/11 characterised by the electroluminescent [EL] layers
• CPC Class Codes: H10K 85/322 comprising boron
• CPC Class Codes: H10K 85/342 comprising iridium
• CPC Class Codes: H10K 85/346 comprising platinum
• CPC Class Codes: H10K 85/658 Organoboranes

Abstract

A dibenzo[1,4]azaborine comprising compound, and devices and formulations including the same are described. The compound includes a ligand L₁ including

• • wherein E₁ is N; E₂ is B; and R₃ and R₄ represent mono, di, tri, tetra substitutions or no substitution;
  • wherein R₁, R₂, R₃ and R₄ are each independently selected from the group consisting of hydrogen, deuterium, halide, alkyl, cycloalkyl, heteroalkyl, arylalkyl, alkoxy, aryloxy, amino, silyl, alkenyl, cycloalkenyl, heteroalkenyl, alkynyl, aryl, heteroaryl, acyl, carbonyl, carboxylic acids, ester, nitrile, isonitrile, sulfanyl, sulfinyl, sulfonyl, phosphino, and combinations thereof;
  • wherein any two adjacent R₁, R₂, R₃, and R₄ are optionally joined to form a ring, which may be further substituted;
  • wherein L₁ is coordinated to a metal M, provided that the metal M does not form bond with E₁ and E₂; and
  • wherein L₁ may be linked with other ligands to comprise a bidentate, tridentate, tetradentate, pentadentate or hexadentate ligand.

Claims

1. A compound comprising a first ligand L₁;

wherein L₁ comprises the following formula;

2. The compound of claim 1, wherein the metal M is a metal selected from the group consisting of Ir, Pt, Re, Os, Ru, Rh, Pd, Cu, Ag, and Au.

3. The compound of claim 1, wherein the metal M is Ir.

4. The compound of claim 1, wherein the metal M is Pt.

5. The compound of claim 1, wherein at least one of R₁ and R₂ is aryl or substituted aryl.

6. The compound of claim 5, wherein at least one of R₁ and R₂ is phenyl, or 2,6-disubstituted phenyl.

7. The compound of claim 1, wherein the compound is homoleptic.

8. The compound of claim 1, wherein the compound is heteroleptic.

9. The compound of claim 8, wherein the compound comprises a second ligand L₂;

wherein the ligand L₂ or part of the ligand L₂ if the ligand is more than bidentate is selected from the group consisting of;

10. The compound of claim 1, wherein the compound having the formula:

11. The compound of claim 10, wherein at least one of R₁, R₂, and R₃ are linked to L₂ to comprise a bidentate, tridentate, tetradentate, pentadentate or hexadentate ligand.

12. The compound of claim 10, wherein the compound is selected from the group consisting of:

13. The compound of claim 12, wherein A is selected from the group consisting of:

14. The compound of claim 10, wherein the compound is selected from the group consisting of:

15. The compound of claim 14, wherein m is 3, and n is 0.

16. The compound of claim 14, wherein m is 1, and n is 2.

17. The compound of claim 14, wherein L₂ is selected from the group consisting of:

18. The compound of claim 10, wherein the compound is selected from the group consisting of:

19. The compound of claim 1, wherein R₁ comprises a 5-membered or 6-membered carbocyclic or heterocyclic aromatic ring;

and

wherein R₁ is coordinated to the metal M.

20. The compound of claim 1, wherein R₂ comprises a 5-membered or 6-membered carbocyclic or heterocyclic aromatic ring;

and

wherein R₂ is coordinated to the metal M.

21. The compound of claim 19, wherein R₁ comprises at least one of the chemical groups selected from the group consisting of:

22. The compound of claim 20, wherein R₂ comprises at least one of the chemical groups selected from the group consisting of:

34. A formulation comprising a compound according to claim 1.

23. A first device comprising a first organic light emitting device, further comprising:

an anode;

a cathode; and

an organic layer, disposed between the anode and the cathode, comprising a compound comprising a ligand L₁;

wherein L₁ comprises the following formula;

24. The first device of claim 23, wherein the first device is a consumer product.

25. The first device of claim 23, wherein the first device is an organic light-emitting device.

26. The first device of claim 23, wherein the first device comprises a lighting panel.

27. The first device of claim 23, wherein the organic layer is an emissive layer and the compound is an emissive dopant.

28. The first device of claim 23, wherein the organic layer is an emissive layer and the compound is a non-emissive dopant.

29. The first device of claim 23, wherein the organic layer further comprises a host.

30. The first device of claim 29, wherein the host comprises a triphenylene containing benzo-fused thiophene or benzo-fused furan;

wherein any substituent in the host is an unfused substituent independently selected from the group consisting of C_n, H_2n+1, OC_nH_2n+1, OAr₁, N(C_nH_2n+1)₂, N(Ar₁)(Ar₂), CH═

CH—

C_nH_2n+1, C≡

C—

C_nH_2n+1, Ar₁, Ar₁—

Ar₂, C_nH_2n—

Ar₁, or no substitution;

wherein n is from 1 to 10; and

wherein Ar₁ and Ar₂ are independently selected from the group consisting of benzene, biphenyl, naphthalene, triphenylene, carbazole, and heteroaromatic analogs thereof.

31. The first device of claim 29, wherein the host comprises at least one of the chemical groups selected from the group consisting of carbazole, dibenzothiphene, dibenzofuran, dibenzoselenophene, azacarbazole, aza-dibenzothiophene, aza-dibenzofuran, and aza-dibenzoselenophene.

32. The first device of claim 29, wherein the host is selected from the group consisting of:

33. The first device of claim 29, wherein the host comprises a metal complex.